62171-64-6Relevant articles and documents
Kinetics of Aminolysis of Phenyl Phenoxyacetates with Benzylamines in Acetonitrile
Koh, Han Joong,Kim, Tae Hyoung,Lee, Bon-Su,Lee, Ikchoon
, p. 2741 - 2751 (2007/10/03)
Kinetic studies are carried out on the reactions of benzylamines with phenyl phenoxyacetates in acetonitrile.Based on (i) the large magnitude of various selectivity parameters, ρx, ρz and ρxz, (ii) the normal kinetic isotope effects (kH/kD > 1.0) involving deuterated benzylamine nucleophiles and (iii) the low entalpies and entropies of activation, it was cocncluded that the reactions proceed by a stepwise mechanism with rate-limiting breakdown of the tetrahedral zwitterionic intermadiate.There are, however, two pathways in the rate-limiting breakdown step of the intermediate, the uncatalysed and base-catalysed.The latter path is characterized by the larger ρxz and kH/kD values, and lower activation parameters than those the uncatalyzed path.